Prospects and Challenges in Organosulfur Chemistry

ACS Sustainable Chemistry & Engineering, Год журнала: 2022, Номер 10(2), С. 671 - 677

Опубликована: Янв. 3, 2022

Sulfur-containing molecules are increasingly crucial in chemistry-related fields and widely applied life science, material food pharmaceutical science. This perspective focuses on the introduction of green sulfurizing reagents sustainable methodologies to realize diverse kinds functionalized transformations synthetic applications. The text is organized according structure sulfur-containing corresponding method. It expected be interest organic chemistry professionals who wish better understand insights applications organosulfur transformations.

Язык: Английский

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Chalcogen bonding in coordination chemistry

Coordination Chemistry Reviews, Год журнала: 2022, Номер 464, С. 214556 - 214556

Опубликована: Апрель 13, 2022

The chalcogen bond (ChB) is defined as a noncovalent interaction between the electron density deficient region (so-called σ or π hole) of covalently bonded atom and nucleophilic (Nu) site in same (intramolecular) another (intermolecular) molecular entity: R–Ch⋯Nu [Ch = O, S, Se Te; R C, Pn (pnictogen), Ch, metal, etc.; Nu lone pair possessing Ha, metal atom, π-system, anion, radical, etc.]. Like halogen (Ha) pnictogen (Pn) bonds, parameters (strength, high directionality tunability) make ChB relevant supramolecular tool design secondary coordination sphere complexes, which concerns an important synthetic strategy improvement functional properties materials. In this review we discuss/illustrate several examples, taken from Cambridge Structural Database, plays crucial role decoration compounds, controlling conformation, packing aggregation tectons, well formation 0D aggregates, 1D chains, 2D layers, 3D frameworks, etc.

Язык: Английский

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Thiophene-based lipids for mRNA delivery to pulmonary and retinal tissues

Proceedings of the National Academy of Sciences, Год журнала: 2024, Номер 121(11)

Опубликована: Март 4, 2024

Lipid nanoparticles (LNPs) largely rely on ionizable lipids to yield successful nucleic acid delivery via electrostatic disruption of the endosomal membrane. Here, we report identification and evaluation containing a thiophene moiety (Thio-lipids). The Thio-lipids can be readily synthesized Gewald reaction, allowing for modular lipid design with functional constituents at various positions ring. Through rational structure, prepared 47 identified some structural criteria required in efficient mRNA (messenger RNA) encapsulation vitro vivo. Notably, none tested have pH-response profile like traditional lipids, potentially due electron delocalization core. Placement tails localization headgroup core endow capability reach tissues. Using high-throughput formulation barcoding techniques, optimized formulations select two top lipids— 20b 29d —and investigated their biodistribution mice. enabled LNPs transfect liver spleen, LNP transfected lung spleen. Unexpectedly, was especially potent retina no acute toxicity, leading photoreceptors retinal pigment epithelium non-human primates.

Язык: Английский

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Multimodal Acridine Photocatalysis Enables Direct Access to Thiols from Carboxylic Acids and Elemental Sulfur

ACS Catalysis, Год журнала: 2024, Номер 14(9), С. 6973 - 6980

Опубликована: Апрель 19, 2024

Development of photocatalytic systems that facilitate mechanistically divergent steps in complex catalytic manifolds by distinct activation modes can enable previously inaccessible synthetic transformations. However, multimodal remain understudied, impeding their implementation methodology. We report herein a access to thiols directly merges the structural diversity carboxylic acids with ready availability elemental sulfur without substrate preactivation. The transformation provides direct radical-mediated segue one most biologically important and synthetically versatile organosulfur functionalities, whose accessibility remains largely dominated two-electron-mediated processes based on toxic uneconomical reagents precursors. two-phase radical process is facilitated reactivity acridine photocatalysis enables both singlet excited state PCET-mediated decarboxylative carbon–sulfur bond formation unknown reductive disulfur cleavage photoinduced hydrogen atom transfer silane–triplet system. study points significant potential providing unexplored directions

Язык: Английский

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Elemental sulphur in the synthesis of sulphur-containing polymers: reaction mechanisms and green prospects

RSC Advances, Год журнала: 2021, Номер 11(15), С. 9008 - 9020

Опубликована: Янв. 1, 2021

The synthesis of polymers using elemental sulphur as a reagent has been studied in relation to the worldwide overproduction cyclo-octasulphur.

Язык: Английский

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Base-Catalyzed Three-Component Reaction between Chalcones, Isothiocyanates, and Sulfur: Access to Thiazole-2-thiones

Organic Letters, Год журнала: 2021, Номер 23(14), С. 5344 - 5348

Опубликована: Июль 6, 2021

ADVERTISEMENT RETURN TO ISSUEPREVLetterNEXTBase-Catalyzed Three-Component Reaction between Chalcones, Isothiocyanates, and Sulfur: Access to Thiazole-2-thionesThanh Binh Nguyen*Thanh NguyenInstitut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Paris-Saclay, 1 avenue la Terrasse, 91198 Gif-sur-Yvette, France*Email: [email protected]More by Thanh Nguyenhttps://orcid.org/0000-0001-8779-9641 Pascal RetailleauPascal RetailleauInstitut FranceMore RetailleauCite this: Org. Lett. 2021, 23, 14, 5344–5348Publication Date (Web):July 6, 2021Publication History Received15 May 2021Published online6 July inissue 16 2021https://pubs.acs.org/doi/10.1021/acs.orglett.1c01653https://doi.org/10.1021/acs.orglett.1c01653rapid-communicationACS PublicationsCopyright © 2021 American Chemical SocietyRequest reuse permissionsArticle Views2499Altmetric-Citations24LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated reflect usage leading up last few days.Citations number other articles citing this article, calculated Crossref daily. Find more information about citation counts.The Altmetric Attention Score is a quantitative measure attention that research has received online. Clicking on donut icon will load page at altmetric.com with additional details score social media presence for given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-AlertscloseSupporting Info (1)»Supporting Information Supporting SUBJECTS:Adducts,Mixtures,Phenyls,Solvents,Sulfur Get e-Alerts

Язык: Английский

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Palladium-Catalyzed Ligand-Directed Divergent Decarboxylative Cycloadditions of Vinyloxazolidine-2,4-diones with 1,3,5-Triazinanes

Organic Letters, Год журнала: 2024, Номер 26(8), С. 1589 - 1594

Опубликована: Фев. 22, 2024

This study demonstrates a highly efficient regiodivergent ligand-controlled palladium-catalyzed cycloaddition reaction of vinyloxazolidine-2,4-diones with 1,3,5-triazinanes. In the presence diphosphine ligand, proceeds via (5+2) pathway to afford 1,3-diazepin-4-ones in excellent yields, while using monophosphine smoothly (3+2) give imidazolidin-4-ones good yields.

Язык: Английский

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Step‐growth Polymerization of Aziridines with Elemental Sulfur: Easy Access to Linear Polysulfides and Their Use as Recyclable Adhesives

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(8)

Опубликована: Янв. 3, 2024

Abstract The bulk radical polymerization of bis(aziridine) with molten elemental sulfur resulted in brittle, cross‐linked polymers. However, when the was treated presence an organobase, ring‐opening reaction aziridine oligosulfide anions occurred, leading to formation linear polymers by step‐growth polymerization. These newly synthesized possess repeating units containing a sulfonamide or amide functional moiety and bonds average segment about two. A small molecular model confirmed nucleophilic addition aziridine. It verified that S−S dynamic bond exchange takes place organic base within chains. mixture polysulfides pyridine exhibits exceptional adhesive properties applied steel, aluminum substrates. Notably, these prepared adhesives displayed good reusability due complete recyclability their solution processability. This sulfur‐involved approach represents innovative method for synthesis advanced sulfur‐containing polymers, demonstrating potential various applications beyond.

Язык: Английский

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Syntheses of Thiophenes – Recent Advances

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(3)

Опубликована: Янв. 27, 2024

Abstract Thiophene, as an important sulfur‐containing heterocyclic, is widely used in pharmaceuticals, functional materials, and natural products. Furthermore, thiophene of great interest to synthetic chemists due its diverse reactivities. Over the past few decades, many strategies are developed for functionalized thiophenes. Several reviews have been reported. However, there no review on synthesis summarized based sulfur sources. The current envisioned summary methods with respect sources give support choose appropriate tools obtain substrates.

Язык: Английский

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Synthesis of α-ketothioamides with elemental sulfur under solvent-free conditions in a mixer mill

RSC Mechanochemistry, Год журнала: 2024, Номер 1(1), С. 38 - 42

Опубликована: Янв. 1, 2024

α-Ketothioamides are formed by a mechanochemical solvent-free Willgeroth–Kindler-type reaction starting from acetophenone derivatives, amines, and elemental sulfur.

Язык: Английский

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